[((3S)-3-Amino-3-carboxy)propyl][(5-nitrothiophen-3-yl)hydroxymethyl]phosphinic Acid

ID: ALA4061423

PubChem CID: 92044496

Max Phase: Preclinical

Molecular Formula: C9H13N2O7PS

Molecular Weight: 324.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCP(=O)(O)C(O)c1csc([N+](=O)[O-])c1)C(=O)O

Standard InChI:  InChI=1S/C9H13N2O7PS/c10-6(8(12)13)1-2-19(17,18)9(14)5-3-7(11(15)16)20-4-5/h3-4,6,9,14H,1-2,10H2,(H,12,13)(H,17,18)/t6-,9?/m0/s1

Standard InChI Key:  GDELUTDICYGXSV-AADKRJSRSA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
    8.1615  -11.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9642  -11.4847    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.3598  -10.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7992  -10.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0616  -10.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3455  -10.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3283   -9.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6465  -10.5512    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.9304  -10.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2314  -10.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5153  -10.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8163  -10.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4981   -9.3703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1002  -10.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8335  -11.4277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6407   -9.7320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6407  -11.3664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1708  -10.6686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6637  -11.3204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4888   -9.9158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  1
 12 14  1  0
 12 15  2  0
  8 16  2  0
  8 17  1  0
  3 18  1  0
 18 19  1  0
 18 20  2  0
M  CHG  2  18   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4061423

   (2S)-2-amino-4-[hydroxy-[hydroxy-(5-nitrothiophen-3-yl)methyl]phosphoryl]butanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 324.25

Molecular Weight (Monoisotopic): 324.0181

AlogP: 0.72

#Rotatable Bonds: 7

Polar Surface Area: 163.99

Molecular Species: ZWITTERION

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.05

CX Basic pKa: 9.53

CX LogP: -2.12

CX LogD: -5.26

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.32

Np Likeness Score: -0.16

References

1. Selvam C, Lemasson IA, Brabet I, Oueslati N, Karaman B, Cabaye A, Tora AS, Commare B, Courtiol T, Cesarini S, McCort-Tranchepain I, Rigault D, Mony L, Bessiron T, McLean H, Leroux FR, Colobert F, Daniel H, Goupil-Lamy A, Bertrand HO, Goudet C, Pin JP, Acher FC..  (2018)  Increased Potency and Selectivity for Group III Metabotropic Glutamate Receptor Agonists Binding at Dual sites.,  61  (5): [PMID:29397723] [10.1021/acs.jmedchem.7b01438]

Source

Source(1):

• Scientific Literature